The Court Jester Of Hip-Hop: Here Are Eminem’s Funniest Moments

Eminem has never been afraid to make fun of himself, whether it be in his raps, in television appearances, or in film. One of the things that makes Marshall Mathers so appealing is his willingness to skewer not only everything in pop culture, but also himself. While he’s known as a bit of a recluse, when the rap superstar does pop up, you can usually bet that he’s not always going to be incredibly serious. Here are nine instances when Eminem brought the funny.

It’s Raining Dicks

In 2009, Em appeared on the German TV show TV Total, and with the lack of censorship in the country, Marshall decided it’d be a good time to pretend like penises were falling from the sky. Host Stefan Raab played along, and the two had a comical exchange for the duration of the interview. Em even broke into an impromptu freestyle over a German tune proving that Slim Shady can rap over any beat.

Confused In Monroe

For fans of Eminem, possibly one of the greatest faux interviews of all-time occurred when Stephen Colbert took over public access TV with his Only in Monroe program in 2015. The segment with Marshall turned into an absurd tapestry, with Colbert offering Em retirement tips and a fallback plan should rap not work out for him.

Teaching Jimmy Kimmel To Rap

Late night TV host Jimmy Kimmel and Eminem have had some fun moments through the past several years, but one of the best segments saw the hip-hop titan teaching Kimmel how to become a rapper. Kimmel even looked the part, dressing in Em’s trademark sweats while rapping through his stage persona “Briefcase Joe.”

Live TV Freaks Marshall Out

Just like his sweatpants swag, Em is known for his absurdist humor, and his appearance during an ESPN college football show proved that. Watch the Oscar-winning rapper deftly put together his fantasy football commentator team while promoting the music video for “Berserk.”

Eminem, Lindsay Lohan, And Triumph

Em had a brief, and tense altercation with Triumph, the Insult Comic Dog at the MTV VMAs one year, but a later appearance by Marshall saw him embody the talking puppet — Eminem manages to insult Lindsay Lohan’s film career before breaking into “Ass Like That.”

Marshall Goes Back To High School

In 2009, Eminem was back on track, beating back his addictions to return to the music scene that he conquered a decade earlier. For the MTV Movie Awards that year, Em also returned to high school for a digital short that saw the rapper pass notes, hit on the teacher, and eventually graduate.

Eminem Does Not Love Ray Romano

For Judd Apatow’s 2009 film, Funny People, Eminem plays himself, bickering with Adam Sandler’s character about the price of fame on his anonymity. Not only can Marshall not attend venues like K-Mart and Chuck E. Cheese, he can’t go to dinner without Ray Romano staring him down. Who the hell is Ray Romano?

He’s Gay?

In 2014’s The Interview, Slim once again plays himself opposite Seth Rogen, but this time, he reveals that he’s gay during a sit-down with James Franco’s character. The scene is one of the funniest moments in the film, and plays off of the media’s fascination with Eminem’s acrimonious past with the LGBT community.

Bruno Crash Lands

Truly proving that he can be the butt of his own jokes, Sacha Baron Cohen and Eminem collaborated to stage this incident that played as if it were an accident. Cohen, as Bruno, descends from the heavens and lands right on Em’s face, crotch first. It’s an amazing moment, and although it was later revealed that it was pre-planned, it officially made Eminem the court jester of hip-hop.

My favorite is the time when he and Mark Wahlberg were both guests on TRL at the same time, and as they were about to go commercial Eminem said something about them standing around like a big fun bunch, to the clear displeasure of Marky Mark, who was then gone when they came back from break.